Patent GB-1235554-A (GB)
Title: Carbamoyloxy anilides and compositions containing the same
IPC: C05C11/00
Filed: 1968-06-18
Abstract: 1,235,554. Carbamoyloxy and thiocarbamoyloxy anilides. MONSANTO CO. 18 June, 1968 [19 June, 1967], No. 29046/68. Heading C2C. [Also in Division A5] The invention relates to 3-(carbamoyloxy) and 3-(thiocarbamoyloxy) anilides of the general formula in which (a) R is a hydrogen atom, a group having the general formula R<SP>2</SP>-[-B-] n - in which B is an oxygen atom or a -CO- group and R<SP>2</SP> is a monovalent aliphatic hydrocarbon group having up to 18 carbon atoms and n is 0 or 1, or R is a group having the general formula R<SP>5</SP>O-[-R<SP>4</SP>O-] m -R<SP>3</SP>- in which R<SP>3</SP> is an alkylene or an alkyleneoxyalkylene group having not more than 8 carbon atoms, R<SP>4</SP> is an alkylene group having not more than 4 carbon atoms, R<SP>5</SP> is an alkyl or alkenyl having not more than 4 carbon atoms and m is 0 or 1; R<SP>1</SP> is a hydrogen atom or a monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon group, a hydrocarbonoxyhydrocarbon group or a haloalkyl group having not more than 18 carbon atoms, Y is a group having one of the formulµ in which each of R<SP>6</SP> and R<SP>7</SP> is a hydrogen atom or an aliphatic, cycloaliphatic or aromatic hydrocarbon group or a hydrocarbonoxyhydrocarbon group having up to 18 carbon atoms, X and X<SP>1</SP> are each halogen atoms, a and b are zero or integers from 1 to 3, each of R<SP>8</SP> and R<SP>9</SP> is an alkylene group having 1 to 6 carbon atoms, provided that not more than 8 carbon atoms are ring carbon atoms and d is 0 or 1, and Z is oxygen or sulphur provided that when R is a hydrogen atom, Z is sulphur; or (b) R is a hydrogen atom, R<SP>1</SP> is a hydrogen atom, a monovalent aromatic hydrocarbon group or a hydrocarbonoxyhydrocarbon group having not more than 18 carbon atoms, Y is as defined under (a) and Z is an oxygen atom; or (c) R is a hydrogen atom, R<SP>1</SP> is an alkenyl group or a monovalent cycloaliphatic group having not more than 18 carbon atoms, Y is a group having the Formula II provided that at least one of R<SP>6</SP> and R is an aromatic hydrocarbon group, and Z is an oxygen atom; or (d) R is a hydrogen atom, R<SP>1</SP> is an alkyl or haloalkyl group having not more than 18 carbon atoms, Y is a group having the Formula II in which each of R<SP>6</SP> and R' is an aromatic hydrocarbon group and Z is oxygen. The compounds may be prepared by reacting an alkali metal derivative of a m-hydroxyacyl anilide of the general formula in which M is an alkali metal with a carbamoyl halide of the general formula Y-C(=Z)-X. The compounds in which Y is -NHR<SP>6</SP>X a  may be prepared by reacting a m-hydroxyacyl anilide of the general formula with an isocyanate or isothiocyanate of the general formula X a R<SP>6</SP>N=C=Z in the presence of a tertiary amine. In an example, 3<SP>1</SP>-hydroxy- 2-methacrylanilide is reacted with ethylisocyanate in the presence of triethylamine to produce 3 - (ethylcarbamoyloxy) - 2 - methoxylanilide. In another example 31-hydroxy propionanilide is reacted with diethylthiocarbamoyl chloride to produce 3<SP>1</SP>-(diethylthiocarbamoyloxy) propionanilide.